How To Answer Some Of Your Most Difficult Job Interview Questions

No matter what industry you’re in or what kind of job you’re hoping to get, chances are that, at some point along the way, you’ll find yourself in a job interview.

Job interviews can sometimes feel like an interrogation, but employers aren’t out to make it easy for you. Interviewers want the right person for the job and, sometimes, that means turning up the heat and grilling candidates.

So we took to Twitter to find out: What is the toughest interview question you’ve ever had to answer?

You asked and Gen Y entrepreneur Anshula Chowdhury was happy to offer some answers.

Before Anshula received her undergraduate degree in economics from the University of Toronto, she had already started her own company. Anshula started the socially motivated venture, Social Asset Measurements, or SAM, in 2010, and has since grown it into a successful business. As her business expanded, she took on many new skills, including learning how to interview job candidates.

Anshula says that when she interviews candidates, she knows what she’s looking for in their responses and offered some insight on how to translate what an employer is asking versus what they really mean.

Here’s Anshula’s take on the some of the interview questions we got from Twitter:

Interview question: What’s your definition of success?

Employers want to provide their staff with an environment where they feel successful, says Anshula, but they can’t do that if you don’t know what “being successful” means to you. She says that when candidates are answering these types of questions, she isn’t looking for the dictionary definition, just something meaningful that demonstrates that they’ve carefully considered what they want out of their career. She adds that answers to this question do not necessarily have to relate back to the job description, they just need to be honest so that interviewer can get a chance to understand you a bit better. Anshula recommends taking the time to carefully consider this question prior to an interview because if a candidate didn’t have any answer to this query, she would automatically consider the interview over.

Interview question: If you could have dinner with anyone, who would it be?

Hardest interview question yet: If you could have dinner with any 3 people of your choice, who would they be? @talentegg

Dinners are a social occasion where friends and family sit together to enjoy a meal and each other’s company. Therefore, when answering this question, Anshula says the important thing is not so much who you place at the table, but why you put them there.

If you say Socrates, elaborate and explain that you’d like to try bantering in Socratic-style or maybe you’d like to sit with Justin Bieber to find out how he managed to use social media to market himself so effectively. Questions like this also show what you’re interested and a bit of your personality in a way that will help employers gauge whether you’ll be a good fit for the office, so be honest and pick ‘em right.

Interview question: What has been the biggest failure in your career so far?

@talentegg what is the biggest mess up you have done in your professional field?

Nobody’s perfect. Your failures show that you tried something, says Anshula, and each letdown comes with a lesson. Saying that you’ve had no failures makes it seem like you’re either lying , haven’t tried enough to fail at something or that haven’t thought carefully about the question. None of which are desirable. Instead, she recommends that you honestly discuss an instance where you’ve failed and focus on how you grew from that experience.

On the flip side, when it comes to sharing your successes, some people are all too ready to step into the spotlight and regale employers with their tales of victory, but Anshula warns that revelling can turn employers off. She says that when she asks about people’s successes, she is looking for candidates to state the accomplishment, why it was meaningful to them and what they learned from it. No more, no less.

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Above all, Anshula says honesty is the best policy. Additionally, the young business owner says it’s important to always remember that you’re interviewing for a job, not spilling secrets with your besties. “An interviewer is not there to listen to anything other than why you’re a good fit for the job,” she says.

Interviewers know when you’re fibbing so take a moment, think about the question and then give an honest, well thought out answer.

About the author

Ishani Nath
is a proud McMaster alum, aspiring writer and current journalism grad student at Ryerson University. When she's not hammering out articles, she can usually be found on a patio or nestled on a couch trying to keep up with those crazy Kardashians. She hopes to one day have a job that makes her excited to get up each morning, or at least one that gives her free food. Intrigued? Enthralled? Learn more by following her on @ishaninath.